Synthesis and Biological Evaluation of 2-Azetidinone & Furan Moiety as Antimicrobial Agents

Abstract

The Novel N1-(3-chloro-2-substituted -4-oxoazetidin-1yl) furan-2-carboxamide 3(a-h) and 1-(2-substituted-5-(furan-2-yl)-1,3,4-oxadiazole-3-(2H)-yl) ethanone 4(a-e) were synthesized as potent antibacterial & antifungal agents. Condensation of furan -2-carbohydrazide(1) with different aromatic aldehydes in presence of glacial acetic acid yielded substituted Schiff base 2(a-h). Cyclocondensation of Schiff’s base with chloroacetyl chloride in the presence of triethylamine resulted in the formation of corresponding target azetidinone 3(a-h). The 2nd series of novel compounds 4(a-e) were synthesized by the cyclization of Schiff’s base using acetic anhydride. These products were evaluated for antibacterial and antifungal activity. N-(3-chloro-2-(3-chlorophenyl)-4-oxoazetidin-1-yl)furan-2-carboxamide (VFA-Cl3), 1-(5-(furan-2-yl)-2-phenyl-1, 3, 4-oxadiazole-3(2H)-yl)ethanone (VFO-b), 1-(5-(furan-2-yl)-2-(4-hydroxyphenyl)-1,3,4-oxadiazole-3(2H)-yl)ethanone (VFO-h4) showed good antibacterial activity against all bacterial strains. N-(3-chloro-2-(4-methoxyphenyl)-4-oxoazetidin-1-yl) furan-2-carboxamide (VFA-m4), 1-(2-(4-fluorophenyl)-5-(furan-2-yl)-1,3,4-oxadiazole-3(2H)-yl) ethanone( VFO-h4) shows significant activity against A. niger and C.albicans. The structures of the newly compounds were confirmed by IR, 1H NMR and mass spectroscopic analysis. Ofloxacin and Fluconazole were used as standard drugs for antibacterial and antifungal activity respectively.